


The first

by CrankyWhenProvoked



Category: Supernatural
Genre: M/M, Weecest, Wincest - Freeform, a list of firsts, slight dub con
Language: English
Status: Completed
Published: 2013-04-28
Updated: 2013-04-28
Packaged: 2017-12-09 18:53:36
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,843
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/776843
Author URL: https://archiveofourown.org/users/CrankyWhenProvoked/pseuds/CrankyWhenProvoked
Summary: <blockquote class="userstuff">
              <p>A look of some firsts for Sam and Dean</p>
            </blockquote>





	The first

~*~The first time Dean kissed Sam it was out of frustration~*~

"But Dean that doesn't make any sense," A young teen Sam said, sitting next to Dean on the couch.

"Will you just drop it or go do it," Dean said, sighing again.

For the past two weeks Sam had been asking him about kissing and first kisses and all things like that. At first Dean had tried telling him what kisses were like, but the younger Winchester still didn't understand. Now it was just getting more and more frustrating that he wouldn't stop asking.

"Because I don't know anyone here good enough to kiss them," He said in a tone that made it seem like kissing was more dirty than it was.

"Well I've tried telling you how it is, but that's not good enough so stop asking please,"

"But Dean," Sam whined a little.

"You know what, fine," Dean said, grabbing the back of Sam's head.

Pulling their lips together, Sam gasped letting Dean flick his tongue in a little. Sam was to startled to do anything, when Dean pulled back panting.

"That is what kisses feel like," He said and stood up, heading to his room.

~*~The first time Dean got a hand job from Sam was because of a bad date~*~

Dean had felt so lucky when the hottest girl on the cheerleading squad said yes to a date, since she was known to put out. So 18 year old Dean took her to some crappy movie at the drive in that was such a chick flick it made his teeth hurt. When they went to a local sex spot in town he thought it was going to make up for it.

However when he had just gotten his hand up her shirt and his lips were near bruised from the kisses, her phone rang. After the near one sided conversation she looked at him and asked to be taken home.

"That was my dad and he wants me home,"

"Ok," Dean said trying not to sound annoyed and to will his erection away.

It was mostly down when he walked in to the small apartment like motel room they were in, but he was still very horny. Going into his room, he quickly shucked his shoes and socks and then his pants and underwear. Lying on his bed he took the cock in his hand and stroked it, trying to conjure up thought, none really working tonight. He was so sick of his own hand, it was almost a month since he had gotten any.

"GAH," He let out a frustrated growl and covered his lower half with his blanket and tossing off his shirt.

"Dean are you ok?" Sam's voice from the other side of his door floated through.

"No," He answered.

Sam opened the door and came into the room, shutting it behind him and moving to sit on the bed, by Dean's legs.

"What's the matter?"

"Nothing really, my date didn't exactly pan out how I had expected," Dean let out a humorless laugh.

"What do you mean?" San asked.

"Don't worry about it kid, just let me be frustrated in piece since there isn't a way for you to help me,"

"What do you mean and don't call me kid,"

Dean let out another laugh. "Unless you can help me with this," Dean threw off the blanket, showing his still slightly pulsing erection. "Then I'm afraid you can't help," He laid his head back into the pillow.

"I could," Sam said softly, reaching out and grasping Dean's cock.

A loud gasping hiss escaped Dean's mouth as Sam's hand fully closed around him. The start of an objection and maybe a curse or two started coming from Dean's mouth until Sam's hand started moving. Sam's hand wasn't nearly as skilled as some of the girls that Dean had had, but at the moment he could care less. It had been to long with just his own hand and he wasn't going to turn down the pleasure.

He only lasted about five minutes with Sam's hand on him before he came with a moan over his chest, stomach and Sam's hand.

"Sammy," He said a little breathlessly.

"Don't mention it," Sam said and stood up, heading out of the room to go and wash his hands.

Dean saw what Sam hadn't wanted him to though, the look of udder shame on his face.

After that night they didn't talk about it and that was their MO and they were just fine with it.

~*~The first time Dean fingered and sucked Sam it was shamefully good for him~*~

Sam had come out as bi to him a few weeks ago and Dean was a little shocked, but he supported him none the less. Even going as far to hide where he had dropped Sam off since at just 16 he couldn't really drive himself. When Dean got a call from Sam asking him to pick him up however, it was a bit of a shock.

"What happened Sammy?" Dean asked when Sam got in the car, looking a bit like a kicked puppy.

"Nothing," He said, looking out the window as Dean started heading back to their 'home'.

"Come on Sammy, tell me,"

Sam just shook his head and Dean let it drop until they were at the house and he followed him into his room.

"You are going to tell me," Dean said, pouncing on Sam and pinning him under him, Sam's arms at his sides.

"Why is it so important that I tell you?" Sam squirmed a little, not really getting far though.

"Because something is obviously bothering you and I'm not going to let it go till you tell me,"

"It's a little embarrassing," Sam said, his cheeks confirming the statement.

"What is it Sammy?"

"Well me and Jack were actually going to go further tonight than before or so I thought from the way he was talking, but when I told him what I wanted he called me a slut and told me to go home,"

"Ah Sammy, I'm sorry," Dean said frowning. "You want me to kick his ass,"

"No, It's ok, I just didn't think it was bad but I guess I was wrong,"

"Don't say that Sammy, I'm sure that he was just being an ass and what you wanted was not wrong at all,"

"You didn't see his face," Sam sighed.

"What did you want?" Dean asked, making Sam jump a little.

"It's ok, you don't have to try and make me feel better, I'll be fine De,"

"Tell me Sammy, so I can pound it into your head that it is NOT wrong,"

Sam blushed more and mumbled something.

"What Sammy?"

"I wanted him to finger me,"

"Is that it? Cuz I gotta say that is how you start the whole gay sex thing,"

"Well that while he was blowing me, Dean I'm sorry," Sam said suddenly as his face got even more red.

Dean looked confused for a second, until he felt Sam's erection poking him in his lower stomach.

"Talking about it getting you excited?" Dean asked, cocking an eyebrow.

"Well this is how we were laying when I told him about what I wanted," Sam blushed.

"Do you still want it?" Dean asked.

"Dean no you can't, were brothers," Sam said as his eyes started holding the same shame they held when he had jerked Dean off.

"I don't care, you helped me out once upon a time and I want to help you,"

"Dean no,"

"To bad," Dean said suddenly sitting up and undoing Sam's pants and pushing them and his boxers off, the younger to stunned to do much.

"Dean," Sam whined as he watched Dean slick up two of his fingers and move them between his legs.

Another objection started coming from Sam's lips, when it was cut off by Dean slipping his middle finger into him, up to the first knuckle. Moving his finger in and out slowly slipping it in further, he moved his head over the head of Sam's cock. Flicking his tongue out, he collected the precome there and then took half of Sam in with one move.

"Dean, this is wrong," Sam said again, moaning however when Dean started moving over him.

As much as he wanted to fight it, his body was reacting and with his eyes closed he could pretend it wasn't Dean. By the time he was close Dean had both fingers in him and was humming around his cock.

"Oh fuck, I'm gonna come De," Sam moaned and did just that.

Dean swallowed it all and sat up slightly, pulling his fingers out of Sam, the younger starting to look shamed again. Giving him a reassuring smile, Dean kissed his hip and got up before Sam could see that he had come with just moving his hips against the bed.

Once again they didn't talk about it.

~*~The first time Dean fucked Sam they were both drunk~*~

"Fuck what did you give me?" 18 year old Sam said as he and Dean stumbled into the hotel room, Sam still in his cap and gown.

"Just something to celebrate, you made it through Sammy," Dean said, running his hand through Sam's hair, knocking the cap off.

"Well I couldn't have done it with out the time's you made dad let us stay so I could be in the same school longer than a few days,"

"Don't mention it," Dean smiled as he pulled Sam into a hug.

The next day he would try to blame it on the alcohol, but the moment he pushed his lips to Sam's it was all he wanted. Sam tried to protest, but the strong alcohol in his system seemed to be saying yes for him.

"Sammy," Dean husked against his lips as he slid the gown off and tossed it with the cap before working to get them both naked.

Almost two hours later, they fell asleep naked, sated and in Sam's case embarrassed.

When Sam left for Stanford Dean had given him a bruising kiss and a hickey when he drove him to the bus station.

~*~The first time Dean tasted an adult Sam it felt like coming home~*~

In the first year after Sam came back to him, Dean didn't try to touch him at all, giving him time to get over Jess. When Sam came out of the bathroom one time, in a towel that barely covered anything, Dean couldn't help himself.

"Dean, No," Sam said, panicking when Dean pushed him against the wall.

"Shut up Sammy," Dean said and pressed their lips together.

It took a while of Dean doing everything to coax Sam into kissing him back, but eventually he did.

"It's wrong Dean," Sam said around a moan when Dean nipped at his neck.

"I don't care if you don't,"

"I do,"

"Then act like it," Dean challenged, grabbing Sam through the towel.

As much as Sam wanted to stop and push Dean away, the older male knew how to push all the right buttons on him. And he was pushing them good.

After that day Dean started taking Sam when ever he got the urge to and Sam let him, never really participating. Each time started feeling like a bit more that he was raping Sam, but the younger Winchester never said stop, so he didn't. He would just lay there and take it, coming when Dean would stroke him so there was some pleasure there, but at times more shame. Sam was never the one to initiate it, but he would never say no.

~*~The first time Sam kissed Dean, it shocked the older male more than anything~*~

"I'm older so I get the first shower," Dean claimed as him and Sam came in from a hunt.

"Sure, sure whatever," Sam said, with a smile. When Dean wasn't being incestual, they were just brothers.

"Bitch," Dean said, heading into the small room.

"Jerk," Sam called out and Dean laughed.

Dean took a relatively quick shower, seeing as Sam needed one to and would bitch if it had to be a cold one. The younger took his own and when he got out and slipped his pajama pants on, he caught a look at himself in the mirror. He didn't want to think that he was getting wrinkles this early in life but that's almost what it felt like he was seeing.

Letting out a small laugh at himself, he really took a look. There were slight bags under his eyes and his whole face didn't look as happy as it once did. He wanted to blame it on what Dean was putting him through but couldn't. Even if Dean was the one causing the pain, he couldn't hate his brother. Looking into his own eyes in the mirror, he let out a sigh and started thinking about a thought that had been in his head for a while now.

Why didn't he ever do anything in bed, it wasn't like it didn't feel good. When Dean would hit his prostate he would see stars, but he never made any noise.

"It's because you think it's wrong," His inner voice whispered, which sounded like a priest friend he knew in Stanford.

"Isn't it though?" He asked himself silently.

"Yes, he's your brother, your own flesh and blood and you let him fuck you in the ass like the whore you are,"

"Shut up," Sam growled in his head. It wasn't just fucking at times to Dean.

There were time's when it was fast and rough and left Sam walking funny for a few days, but there were other times as well. When Dean would kiss Sam softly, sweetly and more make love to him than fuck him.

"It's still wrong. Wrong, wrong, wrong,"

"No it's not,"

"Then why do you think it is if you're trying to defend yourself against yourself,"

Sam let out an amused chuckle at himself that he was indeed arguing with himself over whether or not fucking his brother was wrong.

Letting out a sigh he really thought about it and it slowly didn't seem as wrong anymore to him. Dean was always there and was always one to take care of him, hell he had taken knifes and bullets for him before. He wasn't bad looking either, Sam knew that long before they were ever anything though, but it kinda felt good to admit it.

"I love my brother," Sam whispered into the mirror. "I love him as a … lover,"

As the words fell from his lips, they suddenly felt powerful and he wanted to be in Dean's arms.

Opening the door, he looked around and found Dean slipping his shirt off and tossing it on his bag. Walking over to him, he spun him around and pushing him up against the wall, causing Dean to cry out slightly. Before Dean could say anything Sam's body covered his and his mouth found his as well.

Dean's eyes were wide as Sam's hands found the side's of his neck and their lips stayed pushed together. As he started kissing the taller male back, his hands moved up and rested on Sam's hips. Sam's tongue flicked out and into Dean's mouth causing him to moan and his cock to spring to attention.

"Sammy?" Dean asked questioningly when Sam pulled back for some much needed air, but not letting go of Dean of moving far.

"I love you Dean," Sam said, making Dean's eyes widen again.

"Sam, what has gotten into you?"

Chuckling lightly Sam kissed his lips chastely for a moment, then pulled back again.

"I just thought about us,"

"What do you mean?" Dean said, not quite ready to believe that Sam was going to be a willing participant in what they were doing.

"Us, as boyfriends, lovers, what ever you want to call it,"

"Boyfriends? Sammy, what?"

"Dean I can't keep letting you fuck me,"

"Then why did you kiss me?" Dean asked, a little hurt.

"Because for a while you are not going to fuck me, you are going to make love to me,"

"Sammy are you sure?"

"Dean Winchester," Sam said, making Dean jump.

"Yes?"

"Will you do me the favor of making love to your boyfriend?" Sam asked, rolling his hips forward against Dean's.

"Yes,"

Sam smiled and pulled Dean to the bed pushing him down on it gently, their lips finding each other again. Running his hands up Dean's chest the older male shivered as Sam's lips left his and started for his neck.

"Oh baby boy," Dean gasped as the other male started sucking the skin of his neck.

"Yes Dean?" Sam asked when a pretty good mark was left.

"Just feels damn good having a willing participant in this," Dean said gently, trying not to make Sam suddenly change his mind.

Sam looked a little upset for a moment then leaned in again and gave Dean a chaste kiss.

"I'm sorry it took me so long to get over myself,"

"No," Dean said, holding Sam's hips. "Don't ever say that again, if anyone should say their sorry it's me for taking advantage of you for so long,"

Sam opened his mouth to object but let out a small chuckle instead, making Dean cock an eyebrow at him.

"Care to share with the class what's so funny?"

"That were sitting here in pity when we could just accept that I'm going to be active from now on and working on getting you in my ass in the next few minutes,"

"Now who would argue with that," Dean said and tried to roll them over, just to be stopped by Sam. "What?"

"I want to be on top, something completely new to mark that things will be different,"

If Dean's heart would have swelled anymore, he was sure it was going to burst out of his chest.

"Take me however you want baby boy,"

"Can I suck you?" Sam asked suddenly, making Dean jump and moan.

"Like I would say no,"

Sam smiled and started kissing down Dean's chest, mapping where made him moan and where didn't. Getting to the top of Dean's pants, he could see Dean's excitement and swallowed. He wasn't quite used to the feeling of wanting his brother, but it didn't quell his own want. Slipping the pants and boxers down, he looked with new eyes at Dean's cock, licking his lips lightly. It had never looked so appealing and he leaned forward, brushing his lips right under the head of his cock.

"Fuck Sammy," Dean gasped and shivered and Sam kissed a line down the vein.

"Hmm?"

"Been dreaming about this for so long Sammy," He gasped as Dean wrapped his mouth around the head and sucking softly.

"Fuck," Dean swore once, then a string of them followed as Sam took him in deeper.

He didn't take him deep or was he really good at it, but to Dean it felt better than anything since it was Sammy. His Sammy. That thought almost pushed him over the edge and he would have if Sam hadn't stopped.

"I can't do that anymore, my jaw hurts," Sam said, looking a bit embarrassed.

"It's ok Sammy, come here," Dean said, pulling Sam against him, kissing his jaw.

"Dean please, I want you in me,"

A resounding moan followed the request as Sam stood to get his pants off and Dean grabbed the lube out of the drawer. As Sam crawled back over him, he took the lube from him and popped it open.

"Gonna open myself for you," Sam said in a husky voice as he poured some on his fingers.

"You keep this up and I'm going to come before you even get on me," Dean growled in pleasure as Sam reached back and started working his fingers in.

"Now that would be a shame wouldn't it?" Sam asked, with a sexy eyebrow flick.

"Fuck Sammy," Dean gasped again as the younger Winchester panted and moaned over him.

"Tell me you want it," Sam said, licking his lips as three of his fingers were now in him.

"Sammy you know I want it,"

"That doesn't sound like you're telling me,"

"I want you Sam Winchester, I want you on my cock,"

Sam pulled his fingers out and positioned himself over Dean. "Thought you'd never ask,"

As Sam slipped down his cock, Dean's mind went static-y at the pleasure plus that Sam actually wanted this. When he fully was in Sam, the younger male moaned low in his throat as he started moving up Dean again. When he was almost to the point of pulling out, he slammed back down on Dean, them both moaning at it.

"Fuck yea," Dean moaned.

Sam did this a few more times before getting into a rhythm over Dean, their moans only growing.

"Baby boy," Dean moaned loud as Sam grabbed his hand and put it around his cock.

"Play with me,"

Moving his hand over Sam's cock, the younger male started moaning loudly and came just a few strokes later. With the incoherent mumblings of pleasure and the look of sheer yes on his face, Dean's orgasm followed quickly. Sam collapsed against Dean, breathing hard into his neck as he idly reached for the towel Dean had left there after his shower. Moving off of him and to the side, Sam cleaned them up and tossed the dirtied cloth to the side. Dean stretched a little and made to get up off the bed when Sam pulled him back and against his front.

"Where do you think you're going?" Sam asked, wrapping his arms around Dean's neck.

"To the other bed?"

"Nope, you are staying right here tonight,"

"Sammy, where did this all come from?" Dean asked resting his hand on Sam's hip.

"I was just arguing with myself about it being wrong or not and came to like the fact that it didn't feel wrong anymore,"

"So what is going to happen now?"

"Well we are going to go to sleep tonight and wake up in each others arms or on opposites sides of the bed, we'll have to work with that and you to get over the mushyness of it,"

Dean let out a little chuckle. "I'll do my best,"

"And then we get up and maybe have some fun running the water in the shower cold together," He said with a quirk of his eyebrow.

"Mmmm defiantly can get behind that,"

"Then we go out to get breakfast, you hold my hand and for the rest of our days introduce me as your boyfriend not your brother anymore,"

"I think I can do that are you absolutely sure about it though, you're not going to wake up tomorrow and suddenly never want me to touch you again?"

"I'm sure De," Sam said and pressed their lips together again. "I promise you,"

~*~The first time Sam broke that promise, was never~*~


End file.
